Topiramate

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  • Identifiers

    CAS number
    97240-79-4

    Molecular formula
    C12H21NO8S

    SMILES
    CC1(O[C@@H]2CO[C@@]3([C@H]([C@@H]2O1)OC(O3)(C)C)COS(=O)(=O)N)C

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 69.73%
    Roasted 26.69%
    Meaty 26.57%
    Savory 23.57%
    Cooked 21.2%
    Sulfurous 18.21%
    Milky 13.52%
    Onion 12.39%
    Cooling 12.35%
    Nutty 12.1%

     

    Flavor
    Bitter 66.75%
    Roasted 20.81%
    Cedarleaf 20.24%
    Bouillon 19.9%
    Taco 19.31%
    Scallion 19.31%
    Carrot 19.25%
    Blackberry 19.23%
    Ripe apricot 19.08%
    Boiled shrimp 18.97%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.8

    pKa est.
    9.03 (weak base)

    Molecular weight
    339.36 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 123-125 ºC
    • 125-126 °C
    • 125 - 126 °C

    Boiling point

    • 438.7

    Flash point

    • 245.52 ˚C est.

    Solubility expt.

    • 9.8 mg/mL
    • Soluble in most alkaline solutions containing sodium hydroxide or sodium phosphate and having a pH of 9 to 10. It is freely soluble in acetone, chloroform, dimethylsulfoxide, and ethanol.
    • In water, 9,800 mg/L, temp not specified

  • Synonyms

    • topiramate
    • 97240-79-4
    • Topamax
    • Epitomax
    • Topamax Sprinkle
    • Topina
    • Tipiramate
    • Topiramato
    • Topiramatum
    • Topimax
    • Topomax
    • McN-4853
    • Tipiramato
    • Epitoma
    • Topamac
    • RWJ-17021
    • RWJ-17021-000
    • Sincronil
    • Qudexy
    • Trokendi XR
    • Qudexy XR
    • USL255
    • (-)-topiramate
    • USL-255
    • 2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate
    • EPRONTIA
    • 2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulfamate
    • DTXSID8023688
    • 0H73WJJ391
    • DTXCID103688
    • CHEBI:63631
    • QSYMIA COMPONENT TOPIRAMATE
    • beta-D-Fructopyranose, 2,3:4,5-bis-O-(1-methylethylidene)-, sulfamate
    • [(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methyl sulfamate
    • topiramate tablet
    • [(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.0^{2,6}]dodecan-6-yl]methyl sulfamate
    • McN4853
    • topiramate spinkle
    • ((1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo(7.3.0.0^(2,6))dodecan-6-yl)methyl sulfamate
    • ((1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo(7.3.0.02,6)dodecan-6-yl)methyl sulfamate
    • ((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-5,5a,8a,8b-tetrahydrodi(1,3)dioxolo(4,5-a:5',3'-d)pyran-3a-yl)methyl sulfamate
    • [(3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-5,5a,8a,8b-tetrahydrodi[1,3]dioxolo[4,5-a:5',3'-d]pyran-3a-yl]methyl sulfamate
    • RefChem:56737
    • GlyTouCan:G44123KB
    • 2,3-4,5-bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate
    • N03AX11
    • G44123KB
    • MFCD00865320
    • C12H21NO8S
    • ((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-3a-yl)methyl sulfamate
    • [(3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl]methyl sulfamate
    • Tipiramate [French]
    • Tipiramato [Spanish]
    • Topiramatum [INN-Latin]
    • topiramatum [Latin]
    • Topiramato [INN-Spanish]
    • McN 4853
    • TPM
    • Topiragen
    • Topax
    • ((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl)methyl sulfamate
    • SMR000466325
    • Topiramate (TPM)
    • TOR
    • Topamax (TN)
    • CAS-97240-79-4
    • BRN 5988957
    • UNII-0H73WJJ391
    • s1438
    • Topiramate CRS
    • HSDB 7531
    • McN 4853;RWJ 17021
    • Sulfamate 7
    • 3hku
    • 3lxe
    • USL 255
    • Topiramate [USAN:USP:INN:BAN]
    • NCGC00095181-01
    • Trokendi xr (TN)
    • KS-1122
    • Topiramate (Standard)
    • TOPIRAMATE [MI]
    • TOPIRAMATE [INN]
    • TOPIRAMATE [JAN]
    • Spectrum2_001128
    • TOPIRAMATE [HSDB]
    • TOPIRAMATE [USAN]
    • TOPIRAMATE [VANDF]
    • CBChromo1_000352
    • TOPIRAMATE [MART.]
    • 2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulfamate
    • TOPIRAMATE [USP-RS]
    • TOPIRAMATE [WHO-DD]
    • BIDD:PXR0127
    • SCHEMBL34631
    • BSPBio_002306
    • Topiramate (JAN/USP/INN)
    • Eprontia (liquid formulation)
    • MLS000759431
    • MLS001424070
    • BIDD:GT0854
    • SPECTRUM1505801
    • SPBio_000995
    • CHEMBL220492
    • GTPL6849
    • orb1310396
    • TOPIRAMATE [ORANGE BOOK]
    • BDBM10887
    • HY-B0122R
    • TOPIRAMATE [EP MONOGRAPH]
    • TOPIRAMATE [USP IMPURITY]
    • HMS1922H06
    • HMS2051L09
    • HMS2093D20
    • HMS2232H21
    • HMS3414C15
    • HMS3678C15
    • HMS3715I12
    • HMS3884C17
    • Pharmakon1600-01505801
    • TOPIRAMATE [USP MONOGRAPH]
    • [(3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl]methyl sulfamate (non-preferred name)
    • ALBB-022457
    • HY-B0122
    • MSK10313
    • Topiramate, 1mg/ml in Acetonitrile
    • Tox21_111472
    • 97240-79-4

  • Applications

    Topiramate (CAS 97240-79-4) is used primarily as an active pharmaceutical ingredient (API) in oral dosage forms, formulated into tablets and capsules; it is also evaluated in pharmaceutical research and development as a representative sulfamate-containing compound for formulation and analytical method development; in analytical laboratories, it serves as a reference standard for assay and impurity profiling, and it may be encountered in quality control testing and regulatory submissions related to the ingredient.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 216.33
    methanol 586.83
    isopropanol 86.26
    water 32.39
    ethyl acetate 265.75
    n-propanol 85.39
    acetone 569.48
    n-butanol 51.99
    acetonitrile 375.23
    DMF 1874.01
    toluene 20.95
    isobutanol 36.32
    1,4-dioxane 444.04
    methyl acetate 361.13
    THF 600.43
    2-butanone 254.96
    n-pentanol 33.23
    sec-butanol 40.3
    n-hexane 1.21
    ethylene glycol 191.97
    NMP 1585.73
    cyclohexane 3.38
    DMSO 1855.82
    n-butyl acetate 135.53
    n-octanol 20.2
    chloroform 420.76
    n-propyl acetate 218.09
    acetic acid 1056.77
    dichloromethane 538.2
    cyclohexanone 315.07
    propylene glycol 113.85
    isopropyl acetate 124.81
    DMAc 1465.39
    2-ethoxyethanol 533.11
    isopentanol 30.07
    n-heptane 1.31
    ethyl formate 541.67
    1,2-dichloroethane 253.98
    n-hexanol 29.26
    2-methoxyethanol 880.81
    isobutyl acetate 100.81
    tetrachloromethane 32.28
    n-pentyl acetate 73.84
    transcutol 340.8
    n-heptanol 18.56
    ethylbenzene 12.38
    MIBK 63.3
    2-propoxyethanol 410.58
    tert-butanol 44.33
    MTBE 29.82
    2-butoxyethanol 237.76
    propionic acid 288.37
    o-xylene 15.12
    formic acid 1474.62
    diethyl ether 69.97
    m-xylene 11.46
    p-xylene 20.91
    chlorobenzene 66.78
    dimethyl carbonate 365.85
    n-octane 0.68
    formamide 1736.23
    cyclopentanone 578.99
    2-pentanone 154.01
    anisole 98.06
    cyclopentyl methyl ether 101.85
    gamma-butyrolactone 1184.97
    1-methoxy-2-propanol 408.5
    pyridine 360.22
    3-pentanone 109.38
    furfural 1241.74
    n-dodecane 0.86
    diethylene glycol 447.64
    diisopropyl ether 11.08
    tert-amyl alcohol 29.45
    acetylacetone 370.31
    n-hexadecane 1.02
    acetophenone 169.76
    methyl propionate 286.38
    isopentyl acetate 89.83
    trichloroethylene 599.3
    n-nonanol 19.86
    cyclohexanol 39.7
    benzyl alcohol 106.31
    2-ethylhexanol 17.3
    isooctanol 13.63
    dipropyl ether 36.8
    1,2-dichlorobenzene 82.06
    ethyl lactate 194.77
    propylene carbonate 661.13
    n-methylformamide 1237.66
    2-pentanol 20.06
    n-pentane 1.28
    1-propoxy-2-propanol 167.45
    1-methoxy-2-propyl acetate 202.93
    2-(2-methoxypropoxy) propanol 137.37
    mesitylene 6.78
    ε-caprolactone 431.27
    p-cymene 10.82
    epichlorohydrin 869.6
    1,1,1-trichloroethane 121.22
    2-aminoethanol 199.55
    morpholine-4-carbaldehyde 1520.82
    sulfolane 1184.51
    2,2,4-trimethylpentane 0.64
    2-methyltetrahydrofuran 210.95
    n-hexyl acetate 81.66
    isooctane 0.37
    2-(2-butoxyethoxy)ethanol 180.01
    sec-butyl acetate 91.61
    tert-butyl acetate 81.29
    decalin 1.71
    glycerin 330.79
    diglyme 532.75
    acrylic acid 416.76
    isopropyl myristate 26.74
    n-butyric acid 288.21
    acetyl acetate 297.89
    di(2-ethylhexyl) phthalate 48.01
    ethyl propionate 171.18
    nitromethane 2653.79
    1,2-diethoxyethane 100.34
    benzonitrile 147.83
    trioctyl phosphate 31.98
    1-bromopropane 50.15
    gamma-valerolactone 1487.74
    n-decanol 14.1
    triethyl phosphate 82.22
    4-methyl-2-pentanol 11.04
    propionitrile 128.44
    vinylene carbonate 731.94
    1,1,2-trichlorotrifluoroethane 916.57
    DMS 157.95
    cumene 8.63
    2-octanol 10.35
    2-hexanone 112.55
    octyl acetate 45.3
    limonene 13.62
    1,2-dimethoxyethane 818.3
    ethyl orthosilicate 61.58
    tributyl phosphate 45.45
    diacetone alcohol 121.49
    N,N-dimethylaniline 64.61
    acrylonitrile 299.67
    aniline 72.83
    1,3-propanediol 257.13
    bromobenzene 51.09
    dibromomethane 213.62
    1,1,2,2-tetrachloroethane 380.86
    2-methyl-cyclohexyl acetate 88.61
    tetrabutyl urea 67.95
    diisobutyl methanol 8.21
    2-phenylethanol 86.16
    styrene 17.03
    dioctyl adipate 64.79
    dimethyl sulfate 725.27
    ethyl butyrate 123.34
    methyl lactate 320.39
    butyl lactate 97.67
    diethyl carbonate 123.15
    propanediol butyl ether 129.41
    triethyl orthoformate 95.4
    p-tert-butyltoluene 8.86
    methyl 4-tert-butylbenzoate 100.4
    morpholine 525.57
    tert-butylamine 13.71
    n-dodecanol 10.13
    dimethoxymethane 738.24
    ethylene carbonate 548.04
    cyrene 258.76
    2-ethoxyethyl acetate 156.13
    2-ethylhexyl acetate 74.15
    1,2,4-trichlorobenzene 123.53
    4-methylpyridine 258.61
    dibutyl ether 20.77
    2,6-dimethyl-4-heptanol 8.21
    DEF 349.95
    dimethyl isosorbide 279.85
    tetrachloroethylene 229.1
    eugenol 123.76
    triacetin 157.35
    span 80 87.35
    1,4-butanediol 97.58
    1,1-dichloroethane 147.44
    2-methyl-1-pentanol 21.28
    methyl formate 1240.3
    2-methyl-1-butanol 27.75
    n-decane 1.33
    butyronitrile 113.08
    3,7-dimethyl-1-octanol 16.54
    1-chlorooctane 8.1
    1-chlorotetradecane 3.58
    n-nonane 1.1
    undecane 1.03
    tert-butylcyclohexane 1.07
    cyclooctane 0.99
    cyclopentanol 83.19
    tetrahydropyran 145.85
    tert-amyl methyl ether 26.87
    2,5,8-trioxanonane 288.2
    1-hexene 6.09
    2-isopropoxyethanol 223.77
    2,2,2-trifluoroethanol 634.87
    methyl butyrate 268.58

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction